Levocetirizine

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Levocetirizine
Levocetirizine structure 2.svg
Ball-and-stick model of the levocetirizine molecule
Clinical data
Trade names Xyzal, Levazyr
AHFS/Drugs.com Monograph
MedlinePlus a607056
Pregnancy
category
  • US: B (No risk in non-human studies)
Routes of
administration
By mouth
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
  • US: OTC
Pharmacokinetic data
Bioavailability High
Protein binding 90%
Metabolism Hepatic 14% CYP3A4
Biological half-life 6 to 10 hours
Excretion Renal and fecal
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
Formula C21H25ClN2O3
Molar mass 388.888 g/mol
3D model (JSmol)
 NYesY (what is this?)  (verify)

Levocetirizine (as levocetirizine dihydrochloride) is a third-generation,[1] non-sedating antihistamine, developed from the second-generation antihistamine cetirizine. Chemically, levocetirizine is simply the isolated levorotary enantiomer of cetirizine, which is sold as a racemic mixture.

Medical uses[edit]

Levocetirizine is used for allergy symptoms including watery eyes, runny nose, sneezing, hives, and itching.[2] The manufacturers claim it to be more effective with fewer side effects than previous second-generation drugs; however, there have been no published studies supporting this assertion. A study part-funded by the manufacturer UCB concluded it may be more effective than some other second- and third-generation anti-histamines, but did not compare it to cetirizine.[3]

Side effects[edit]

Levocetirizine is called a non-sedating antihistamine as it does not enter the brain in significant amounts, and is therefore unlikely to cause drowsiness. However, some people may experience some slight sleepiness, headache, mouth dryness, lightheadedness, vision problems (mainly blurred vision), palpitations and fatigue.[4]

Pharmacology[edit]

Levocetirizine is an antihistamine. It acts as an inverse agonist that decreases activity at histamine H1 receptors. This in turn prevents the release of other allergy chemicals and increase the blood supply to the area, and provides relief from the typical symptoms of hay fever. It does not prevent the actual release of histamine from mast cells.

Chemistry[edit]

Chemically, levocetirizine is the active levorotary enantiomer of cetirizine, also called the l-enantiomer of cetirizine. It is a member of the diphenylmethylpiperazine group of antihistamines.

History[edit]

Levocetirizine was first launched in 2001 by Belgian pharmaceutical company UCB.

Society and culture[edit]

Availability[edit]

On 31 January 2017, the Food and Drug Administration approved Xyzal as an over-the-counter drug.[5] Although the drug was only authorized by the FDA on 25 May 2007, it was already available in most European countries. Like many new drugs it entered the market at a higher price than currently available third and second generation antihistamines. In India, one form of the drug is available as Crohist MK tablets and syrup, a formulation of levocetirizine hydrochloride and montelukast. In India, Crohist MK is a Schedule 'H' drug and may only be prescribed by a registered medical practitioner. In Finland, Hungary, China, The United States and Kuwait[6] the drug is sold over-the-counter.

Brand names[edit]

Different brands (Actavis, Glenmark, UCB) Levocetirizine tablets and oral solution.

Levocetirizine is sold under the following brand names:

  • Xyzal /ˈzzæl/ in Australia, Austria, Croatia, Czech Republic, Finland, France, India, Ireland (also Rinozal), Italy, Lithuania, Netherlands, Poland, Portugal, Romania, Taiwan, Thailand, Turkey, The Philippines, Serbia, Slovakia, Slovenia, South Africa and UK. On May 25, 2007, the United States Food and Drug Administration approved Xyzal, where it is co-marketed by Sanofi-Aventis.
  • Xusal in Germany;
  • Xozal in Greece;
  • Xazal in Spain;
  • Xuzal in Mexico;
  • In Hungary it is marketed as Zilola (made by Richter Gedeon) and Histisynt (Actavis).
  • In India, levocetirizine is marketed by GlaxoSmithKline under the brand name Vozet. Torrent Pharma launched UVNIL for the rural market. Kaptab Pharmaceuticals markets mouth dissolving form in India.
  • In Pakistan levocetirizine was first launched in a liquid formulation by Novartis Consumer Health Division under the name of T-Day Syrup.
  • In Nepal levocetirizine is available in tablet with brand name Curin manufactured by Beximco Pharma.[7]
  • In Chile, it is marketed as Zival and made by Laboratorio Saval.
  • In Sweden, which has a socialized health care system, the Swedish government will not pay for Xyzal, and it has been withdrawn from the market.[8]

References[edit]

  1. ^ Wallace, DV; Dykewicz, MS; Bernstein, DI; Blessing-Moore, J; Cox, L; Khan, DA; Lang, DM; Nicklas, RA; Oppenheimer, J; Portnoy, JM; Randolph, CC; Schuller, D; Spector, SL; Tilles, SA (Dec 2008). "The diagnosis and management of rhinitis: an updated practice parameter". J Allergy Clin Immunol. 122 (6): 1237. PMID 18662584. doi:10.1016/j.jaci.2008.06.003. Retrieved 10 April 2017.  More than one of |pages= and |page= specified (help)
  2. ^ "Levocetirizine Oral". WebMD. 
  3. ^ Grant JA, Riethuisen JM, Moulaert B, DeVos C (2002). "A double-blind, randomized, single-dose, crossover comparison of levocetirizine with ebastine, fexofenadine, loratadine, mizolastine, and placebo: suppression of histamine-induced wheal-and-flare response during 24 hours in healthy male subjects". Ann. Allergy Asthma Immunol. 88 (2): 190–7. PMID 11868924. doi:10.1016/S1081-1206(10)61995-3. 
  4. ^ XOZAL technical specifications booklet.
  5. ^ "Prescription to Over-the-Counter (OTC) Switch List". Retrieved February 9, 2017. 
  6. ^ On different names: http://www.hazipatika.com/gyogyszerkereso/termek/sefaller_5_mg_filmtabletta/54120
  7. ^ "Curin". Archived from the original on October 22, 2012. Retrieved August 29, 2012. 
  8. ^ http://www.fass.se/LIF/substance?substanceId=ID11EHWRUFGBA53CSR

External links[edit]